


Anything You Can Do

by kittenofdoomage



Category: Supernatural
Genre: Anal Sex, Double Penetration, Established Relationship, F/M, Fluff, Oral Sex, Smut, Threesome
Language: English
Status: Completed
Published: 2019-12-04
Updated: 2019-12-04
Packaged: 2021-02-25 22:49:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,067
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21673141
Author URL: https://archiveofourown.org/users/kittenofdoomage/pseuds/kittenofdoomage
Summary: Sam’s feeling frisky while he thinks you’re alone, only for Dean to rudely interrupt.
Relationships: Dean Winchester/Reader, Sam Winchester/Reader
Comments: 4
Kudos: 135





	Anything You Can Do

"Dean’s not here."

Sam’s hands slipped around your waist and you grinned, entwining your fingers with his as he held you. He placed a soft kiss to your neck, and you shivered. It never took much for him to turn you on, and judging by the hardness pressing into your lower back, it didn’t take much for him to get worked up either. You’d been dating the younger Winchester brother for a few weeks now, ever since you’d met on a hunt and connected on some level you hadn’t known existed.

It didn’t hurt that his brother was easy on the eyes as well. Not that you’d let that slip to Sam.

"Dean could be back at any moment," you replied, turning in his arms.

Sam shrugged. "So. We’ll go to my room. Please, Y/N. I want you. Right now." He ground against you, and yeah, he was definitely in a wanting mood. You grinned, standing on tiptoes to kiss his lips softly, only to find yourself swept up in his arms as he carried you to his room. He gently lay you on his bed, pulling your sneakers off, and unbuttoning your pants. "Fuck, you’re sexy." He smiled, slipping your panties over your hips.

"And you’re eager," you gasped, as he touched his tongue to your slit, drawing it slowly up toward your clit, making you whimper. "Fuck, Sam."

"You will in a minute." He chuckled against your cunt, before sliding a single finger inside you. He pumped it a few times, then replaced it with his tongue, delving as deeply as he could, his hands clenched around your thighs, pulling you closer as you grunted and arched underneath, desperately trying to hold off your orgasm.

A cough from the door made Sam pause, and your head snapped to the side to see who it was. Dean leaned against the door frame, his arms over his chest, a lewd grin on his face as he watched the both of you. Sam rolled his eyes, moving to shield you from his brother’s eyes.

"Awww, Sammy, don’t be such a spoilsport," the elder Winchester laughed, "looks like you need a few pointers." You glared at him, trying to ignore the flare of arousal that joined the crescendo Sam had already induced.

"Get lost, Dean," Sam ground out, scowling. Dean tutted, dropping arms to his sides.

"Come on, Sam. Wouldn’t be the first time you’ve needed help with a girl."

Sam was full on glaring now, his teeth ground together. "What, you think you could make her come quicker?" The words were out before he could retract them, and you blushed furiously, moving to sit up a little. Dean took a few steps forward.

"Is that a challenge?" he asked his little brother, and Sam’s eyes moved to yours quickly. You had a decision to make - you could deny this ever happened and ignored the raging crush you had on Dean while dating Sam, or you could let them have their little spat, and have both brothers. Either one had pros and cons, and you had about a second to decide. "Obviously, not without your permission, Y/N," Dean said, his eyes also going to yours.

"You’re such a gentleman," you replied sarcastically.

"Y/N, you don’t have to do anything you don’t want to," Sam muttered under his breath, his hand on your bare thigh. You bit your lip, looking from him to Dean, feeling the desire for both but not wanting to upset him. Sam smiled reassuringly, his thumb caressing your skin. "And it’s okay if you do want to."

"You’re sure?" you whispered, and Dean grinned, sensing his permission. Sam rolled his eyes but smiled all the same, standing from the bed, no longer obscuring you from sight. Your gaze moved to Dean, who smirked when you nodded, removing his jacket as he moved across the room towards you. 

Climbing onto the other side of you, Sam made quick work of helping you remove your t-shirt so you were naked. Dean stood at the foot of the bed, admiring the view. "It’s typical you’d want to date him," he muttered, "but I bet I can make you cum harder."

Sam barked a laugh and your cheeks heated up, knowing exactly how hard he’d made you cum in the past, and doubting Dean would be able to beat it. He might match it though; you weren’t going to argue with him trying at any rate. 

"Have at her." Sam gestured towards you and Dean instantly shooed him off the bed.

"No unfair advantages. You can’t touch her," he instructed - Sam rolled his eyes again, moving to take a seat on the chair diagonally opposite the bed. He unbuttoned his pants, groaning when the pressure against his dick was released, his eyes locked on yours, not flinching as he withdrew his cock into his hand.

Dean’s lips touched your inner thigh and you jumped, not expecting it. The action dragged your attention from where Sam was touching himself and Dean chuckled against your leg, pleased that he’d distracted you. Slowly he kissed a path up along thigh and then up the other, avoiding your pussy, and you gasped at the teasing touch, growing wetter by the second. "Hope you’re enjoying the show, baby brother. Cos she’s wet as hell already."

"She was already wet before you got here," Sam grunted, continuing to stroke himself as he watched his brother between your thighs. "You’re not impressing me so far. She hasn’t made a sound."

Dean scowled, then bent his head, gently teasing at your folds with his tongue - you gasped again, thrusting your hips against him a little. "Hmmm," he moaned. "You taste amazing." He held your thighs apart, slipping his tongue inside you as far as he could, fucking you slowly, and you cried out, writhing underneath him. 

Sam continued to watch, his eyes on your breasts as you moved, his hand stimulating his cock while his brother licked you out.

"That’s a bit better," he mumbled breathlessly. 

Dean was too busy tongue fucking you into the mattress to reply, occasionally flicking your clit to make you cry out. It wasn’t long before you were fisting your hands in Sam’s bed sheets, crying out your orgasm as Dean brought you off, lapping up your juices. When you were done, he pulled up to his knees, his obvious erection tenting the front of his pants.

"Nice effort," Sam comment, standing to move over to the bed, kicking off his boots and pants as he went. "My turn."

Dean slid from the bed, walking around and taking the seat Sam had been using. Just as his brother had done, he pulled his cock free from his pants, stroking it as he watched you on the bed. Sam cupped your pussy with his hand, kissing you firmly as his middle finger slipped inside, making you cry out again as he caressed your sensitive flesh. He broke the kiss, lowering his head to your left breast, sucking the nipple into his mouth, pushing a second finger inside you. Crying out at the unexpected addition, you shivered when his thumb located your clit, small whimpers breaking from your throat as his teeth scraped the sensitive bud in his mouth. 

"Sammy!" You rutted against him, seeking more friction as the climax built inside you. "Sam, please!" He added a third finger, curling them up to touch that sensitive spot, prompting a shrill scream to leave your lips. Your hand fisted in his hair as he continued to pound his fingers into you relentlessly, prolonging the pleasure for as long as he could.

When your screams had returned to whimpers and your body was trembling from the orgasm, Sam pulled away, grinning over at his brother triumphantly. Dean rolled his eyes, his hand still stroking his cock, and he stood, undressing. Sam followed suit as you lay there bonelessly, recovering from the two orgasms the boys had drawn from you.

"How do you want this?" Sam’s voice in your ear made you jump a little, and you smiled up at him.

"You mean I get both of you at the same time?" Your voice was breezy, and to be honest, you felt a little drunk on the sensations still pooling in your stomach. "Well, if that isn’t every girl’s fantasy." Sam raised an eyebrow as you reached out to the bedside table. “Be gentle with me, boys.”

"Wanna toss a coin, Sammy?" Dean smirked, pulling the lube out from the bedside table.

"I won. My choice, I think." Sam grinned back, dragging you against his body. He kissed you deeply, pinning one of your arms underneath him around his waist and the other he pulled up to drape over him. His fingers teased at your folds again before he smoothly swiped the head of his cock over your slit; you shuddered, biting your bottom lip. "I know where I want to be," he whispered, sliding his cock halfway inside you. 

You groaned, feeling the mattress move under Dean’s weight behind you. Warmth settled at your back, Dean’s hands coming up to cup your breasts. Sam kissed you again, pushing further inside you, setting a slow rhythm. Your walls clenched around him and he moaned into your mouth, clutching at your thigh where it rested on his side.

Fingers slipping between your asscheeks made you whimper into the kiss, feeling the cool slick of lubricant as Dean prepped you. It wasn’t your first encounter with anal sex but it was nice that he didn’t want to just dive right in.

His middle finger probed your hole, increased the pleasure that was already spiraling out of control with Sam’s slow thrusts. When he pressed the single digit into you, you sucked in a harsh breath, clinging to Sam’s shoulders with your nails.

By the time Dean had worked up to two fingers, you were begging and panting, practically bouncing between the two of them. Your desperation for more was contagious - Dean withdrew his fingers, spreading a generous amount of the slick gel over his shaft.

Lining himself up with your ass, he pushed against you, grunting at the tightness as he thrust the head of his cock through the first ring of muscle. You cried out, only for Sam to swallow the sound with his kisses, and Dean paused, allowing you a moment to adjust.

Both Winchesters sported impressive cocks, and when they were both finally buried to the hilt inside you, the feeling of bliss that spread through your body, the sensation of two of them impaling you - it was beyond overwhelming.

Sam moved again, continuing his long slow thrusts, as Dean started his own rhythm, timing it against his brother’s so you were always filled by one of them. With every stroke, Sam hit your g-spot, the deepest parts of you, and the feeling was only accentuated by Dean’s accompanying thrust. Every time it happened, you unravelled a little more, coming apart between the two men, feeling like you were no longer a single person, that you were irrevocably connected to them, their bodies an extension of your own. You’d lost track of whose hands were whose, whose lips were whose, your head thrown back in ecstasy and your eyes shut as they continued to fuck you in tandem.

With a throaty cry, Sam thrust hard inside you, causing you to shriek as you felt the thick warmth of his cum filling you, his head against your collarbone as he finished. Dean followed suit, pumping hard into you, one of his hands in your hair as he finished, and the three of you collapsed into a sweaty and satisfied mess on the bed.

Dean pulled away first, leaving you with a small kiss on the back of your neck. Sam withdrew, holding you close to him and his brother chuckled.

"You win, Sammy." Dean pulled his jeans on, glancing over at you as you snuggled further into Sam, the exhaustion taking precedence over anything else. "But at least she’s up for some fun."

Sam rolled his eyes for the umpteenth time, before pulling the sheets over you both. "Don’t be expecting this too often, Dean."

"Oh, I won’t, little brother." Dean grinned, shooting you a wink where you were curled into Sam’s chest. "But you gotta admit – it’s fun to relive the old days."


End file.
